Fashion has always played a pivotal role at the Kentucky Derby. After attending renowned Derby races in England and Paris in 1872, Col. Meriwether Lewis Clark Jr. decided to establish a similar prestigious horse race in America. He secured funding for a racetrack and founded Churchill Downs just outside Louisville, Kentucky, where the inaugural Kentucky Derby took place in 1875. The event has since become synonymous with high stakes and style, drawing enthusiasts from around the globe to this site, a prominent betting platform for Derby enthusiasts.
1910s
Kentucky Derby Fashion has seen its share of eccentric trends over the years, but none as peculiar as the “hobble skirt.” Named after the device used to restrict a horse’s movement, this snug-fitting garment tightly hugged the legs and ankles, dominating fashion from 1910 to 1913.
1920s
The 1920s brought a dramatic shift with the emergence of the “Flapper” look. This era saw the introduction of smaller cloche and bucket hats paired with dresses, gloves, or loose suits. While the daytime Derby events didn’t fully embrace the flapper style, attendees showcased formal suits or dresses adorned with a variety of fashionable hats.
1930s
Hats and headpieces in the 1930s embraced simplicity, blending seamlessly with contemporary fashion trends. Loose-fitting suits and form-fitting dresses, particularly the “slip-on dress,” were popular, complemented by elegant cloche hats, elbow-length gloves, and corsages worn as accessories.
1940s
Celebrities and style icons of the 1940s, such as Carole Landis and Rita Hayworth, set fashion trends with formal suits rather than day dresses. Outfits were sophisticated and coordinated, often paired with matching hats and gloves.
1950s
Until the 1950s, the focus at the Derby was primarily on the winning horse rather than fashion. However, post-war America brought a wave of women eager to dress for high society. The opening of Millionaire’s Row further glamorized the event, showcasing glamorous dresses crafted from taffeta, lace, netting, or chiffon. Tea-length dresses were prevalent, accompanied by cat-eye sunglasses. Conservative styles persisted until the 1960s when a shift towards relaxed attire began to take hold.
1960s
The 1960s marked a period of excitement in Western fashion. Hat brims widened, designs became more creative, and the influence of the West Coast hippie movement encouraged bolder expressions in fashion. The burgeoning feminist movement prompted a departure from traditional outfits to embrace edgier looks, including pantsuits and miniskirts. Fashion icons like Brigitte Bardot, Mary Quant, and Jackie Kennedy defined the decade’s style.
1970s
Building on the relaxed styles of the 1960s, the 1970s brought an attitude to the Derby fashion scene. Women flaunted daringly short skirts and trapeze dresses paired with fedoras or “floppy” sun hats. Despite modern trends, some women sought to uphold Derby traditions, resulting in the resurgence of larger, more elaborate headpieces.
1980s
The 1980s saw the Kentucky Derby gain even more popularity among the rich and famous. Actors and celebrities flocked to Louisville to showcase their elaborate hats. Princess Diana’s influence, particularly her John Boyd hats, contributed to the era’s oversized hat trend. Loose-fitting frocks and short cocktail dresses epitomized the decade’s exuberance and free-spirited fashion.
1990s
Hat styles continued to evolve in the 1990s with an emphasis on bold shapes and accessories. Some Derby attendees embraced humor with whimsical, handmade hat designs, while dresses replaced dress suits as the preferred attire for ladies.
2000s +
Despite a decline in hats as a cultural fashion trend, the Kentucky Derby remains a bastion of tradition and style. In the 2000s, attendees sported ethereal cotton sundresses, vibrant skirts, and even jumpsuits adorned with extravagant headpieces. Dresses in a kaleidoscope of colors and bold patterns created a striking spectacle at Churchill Downs on the first Saturday of May.
Thanks to the influence of Kate Middleton and Prince William’s royal wedding, meticulously designed fascinators and elaborate headpieces enjoyed a resurgence. The Kentucky Derby now stands as a premier event for milliners worldwide.
